jones reagent in acetone 1) 0 deg C, 1 h, 2) r.t., 1 h;

1: 72.5 percent / NaNH2, 1,3-diaminopropane / various solvent(s) / 2 h / 80 °C 2: 95 percent / 1.) n-butyllithium / 1.) hexane, THF, -10 deg C 2.) hexane, THF, 0 deg C, 30 min 3: NaNH2 / liquid ammonia; tetrahydrofuran / 0.5 h View Scheme

1: 72.5 percent / NaNH2, 1,3-diaminopropane / various solvent(s) / 2 h / 80 °C 2: 95 percent / 1.) n-butyllithium / 1.) hexane, THF, -10 deg C 2.) hexane, THF, 0 deg C, 30 min 3: 1.) NaNH2 2.) H2 / 2.) P-2 nickel / 1.) liq. ammonia, THF, 30 min View Scheme

1: 62 percent / Jones reagent / acetone / 1) 0 deg C, 1 h, 2) r.t., 1 h 2: 79 percent / PdCl2(MeCN)2 / tetrahydrofuran / 3 h / Heating; other solvents or solvent mixtures, other times, other β,γ-acetylenic ketones View Scheme